This invention relates to improved methods of reducing friction losses of organic based liquids flowing through confining conduits such as in internal combustion engines, fracturing fluids employed to treat Subterranean formation, metal working fluid and the like. Representative art relating to these types of compounds, their preparation and use are found in U.S. Pat. Nos. 2,245,649; 2,274,302; 2,329,707; 2,346,155; 2,885,417; 2,905,683; 2,983,678; 2,983,679; 3,010,903; 3,331,896; 3,470,222; 3,494,949; 3,505,374; 3,547,820; 3,575,859; 3,706,822; 3,584,087 and 3,757,864, the teachings of which are specifically incorporated herein by reference.
Organic phosphoric acid esters have been employed in their free acid form and/or salts thereof as detergents, lubricating liquids, corrosion inhibitors, friction reducing agents, thickening agents and the like.
U.S. Pat. No. 3,757,864 teaches that certain aluminum salts of organic phosphoric acid esters are useful as friction reducing and gelling agents for nonpolar organic liquids. The salts are formed by reacting a basic aluminum compound with an ester which has been formed by reacting one or more monohydric aliphatic alcohols with a phosphorous compound such as P.sub.2 O.sub.5, phosphorous oxychloride, PCl.sub.5, PF.sub.5 and the like.
It has now been discovered that certain metal salts of complex reaction products of a hydroxy ether and a phosphorous compound such as P.sub.2 O.sub.5 are at least as effective as, and in many instances more effective than, the agents disclosed in U.S. Pat. No. 3,757,864 to reduce friction loss of refined oils and certain crude oils flowing through a confining conduit.